


Chance Encounter

by fuckingcommissions



Series: Ash Ketchum's Harem [1]
Category: Pocket Monsters | Pokemon - All Media Types
Genre: F/F, F/M, Omorashi, Vaginal Sex, commission, holding contest
Language: English
Status: Completed
Published: 2017-05-23
Updated: 2017-05-23
Packaged: 2018-11-04 04:44:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,634
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10983630
Author URL: https://archiveofourown.org/users/fuckingcommissions/pseuds/fuckingcommissions
Summary: Five friends encounter one another at a Pokecenter, and four decide it's time to make a change.





	1. Chapter 1

Ash, Misty, May, Dawn, and Iris all happened to be in the same Pokemon Center, by some strange course of events, and the five of them were all happy to see one another, but all happiest to see Ash. They spent a lot of time getting caught up before it hit them all just how tired they really were. After all, they had come there to rest, and that was what they needed to do. It came time for them to go their separate ways and get rooms, but as Ash went off to his, the girls decided that they would save space by having a slumber party. Not only would there be more rooms available for others, but they wouldn't have to stop getting caught up.

So the four girls got a room together, quickly changing into their nightclothes. May wore a flannel nightgown, Misty wore a yellow tank top and light blue shorts, Dawn wore a pink nightgown, and Iris wore a pink tank top and pink shorts. They all settled in together, talking about their travels and sharing all sorts of stories about the road. Eventually, Ash came up, and it was May who admitted, “I used to have such a huge crush on him.”

“Really?” asked Dawn, looking a little surprised. “I mean, me too, but I never said anything because he was so...”

“Oblivious?” interrupted Iris. “Because that was my problem with him. That boy is completely clueless about those sort of things.”

“No way, you too?” Dawn asked, staring at Iris.

“Seems to be pretty common,” she replied.

“Yeah,” said May, turning to Misty with a grin. “Come on, what about you?”

Blushing, she glanced off to the side and muttered, “I mean, we did spend a lot of time together so I guess...”

“And he _never_ noticed with any of you?” Dawn shook her head in disbelief. “Wow, I can't believe it. I knew he was clueless, but I didn't know he was that clueless!”

“It's not like I didn't try,” groaned May. “And, boy, did I ever try. I tried all sorts of crazy things to get him to notice, but nope! Not even a hint of interest!”

“I know what you mean.” Misty sighed. “It didn't matter what I did. I don't think the boy's interested in anything outside of Pokemon.”

“I bet I tried way crazier stuff than either of you,” said Iris, laughing.

“And I bet I could give all of you a run for your money!” added Dawn.

They went back and forth after that, sharing their stories about different experiences they had trying to get Ash's attention. It started out pretty tame, and they only talked about different outfits they wore. They'd describe whatever excuse they had for wearing such a thing, and then groan over the fact that Ash either didn't notice it or that it really didn't change much of anything. It didn't matter how they dressed, his attention wasn't swayed by any of it.

The only time he really seemed to pay special attention to them were with matters involving Pokemon, and even then, it was strictly platonic. One of them mentioned that he must like something more unusual, and that was when they really began to open up about the things they'd done, even the more shameful ones.

Dawn confessed to leaving her shoes off whenever they were alone, posing in such ways that really showed off her feet in the hope that he was into that, and May recounted the time that “accidentally” let a pair of panties get lost around camp.

“But what if we tried...” One of them started, and it seemed that no matter what they came up with, they would be met with the response of, “I tried that! It didn't get so much as a reaction out of him,” or “been there, done that,” or, “I did that for an entire week, and he didn't seem to notice at all.”

They had all run into the same problem, over and over and over again in their attempts to get Ash to figure out how they felt about him. No one had been able to come up with anything for him, and no one had been able to actually win the dense boy over, and the longer the night went on, the more frustrated they all became as they remembered all their failed attempts.

And the longer the night went on, the more they all remembered just how much they wanted to be the one to make Ash crack, until they were really trying to come up with something to do. It had not been spoken aloud, but they all knew that at least one of them would try to win him over that night. It really spoke to their camaraderie in the matter, knowing that each of them would have supported any of the other girls equally.

“What about...” Misty paused, before finally coming out and saying what had been on her mind. She'd thought about it before in the past, but had never had the guts to try it, and was a bit ashamed to admit her interest in it. But they were all working together, and they were willing to try _anything_. “What about desperation and wetting?”

For those who didn't fully understand what she meant, she got some assistance in explaining it from those who did. There was a pause as everyone truly considered this, and considered what it meant that it was something that nobody had ever tried for him before. And, what was more, they all considered their reactions to hearing it, and each girl had more of an interest in it than they had expected.

“I would be willing to try something like that,” Dawn said finally, breaking the silence.  
“Me too,” replied May, and Iris nodded.

“I just thought it would be a little embarrassing,” said Misty, “but maybe...maybe it might work.”

“So, how are we going to do this?” asked Dawn, and it had already been decided that they were going to do this. “I mean, if all of us are willing to try it...how do we decide who gets to actually do it?”

They talked it out then, because that really was a very important question. Going back and forth, each one insisting why they should be the one to get to do it, they finally reached a decision. Finally, they settled on something; they would have a holding contest, and whoever lasted the longest would go to Ash's room to wet for him, and if he liked it, then they would have their chance with him.

After a little bit more discussion, the four realized just how much they wouldn't mind sharing him. They had grown close over just this one night, and they agreed that the winner should try to convince him to make them all into his harem.

 


	2. Chapter 2

In order to get things started, Misty went to fetch drinks for everyone. None of them were completely empty, so they weren't starting from nothing, but if they wanted things to get serious, they were going to have to speed up the process quite a bit. The four of them took turns drinking, until it became a bit more noticeable that they were all starting to get desperate.

Iris was the first to make her need visible, squirming a bit where she sat. “I don't know if this was such a good idea,” she joked, and they all laughed nervously. It was difficult to get up the nerve to do something like this in a group, and the longer this went on, the more serious they realized it had become.

Iris had started to notice that she needed to pee as soon as the subject of holding and wetting had come up. Once she had actually thought about it, she realized that she hadn't been to the bathroom recently, and her need had been in the forefront of her mind ever since. She was almost reluctant to agree to this contest, simply because she knew that she had no chance of winning.

She looked over the room, watching the others for any signs that they were in as bad of shape as she was, but all she got was sympathetic glances as she crossed her legs and struggled to hold on. It was a while before anyone else showed off their own desperation, and by then, her bladder was absolutely aching for relief.

May let out a small squeak, blushing as she squeezed her thighs together. She was really starting to feel the effect of all that she had had to drink, but she was determined to ignore it for as long as she could. If she had any chance of winning this, she was going to try as hard as she could. She wanted Ash just as badly as everyone else, and though she wouldn't be hurt if it weren't her, she definitely hoped that it would be.

Misty, meanwhile, was doing all she could to keep herself calm, knowing that getting nervous would only speed things up. Her bladder was steadily filling up, but she was tougher than that, and if she did what she could to remain calm, she stood a chance of winning this. She could at least tell that she stood a much better chance than Iris currently did.

The poor girl was already to the point where she couldn't even try to sit still, biting her lip hard and whimpering as she struggled to hold on. Even jamming her hands between her legs didn't do much to help her out, and it seemed that she wouldn't be able to last much longer at all. She looked close to tears just from the strain of holding on, and just looking at her made it a little difficult to ignore the growing pressure. Misty quickly looked away.

Dawn was surprised at how well she was holding up. She could already tell that the other girls were struggling, and though she could tell that it was getting bad for her, it seemed that it was worse for all of them. Iris would be out of the game in no time, and she was sure that Misty and May couldn't be that far behind. If Dawn could hold out long enough, she really could be the one to win, and she steeled herself, vowing to make it to the end. If she wasn't the winner, she would at least strive for second place, if only for the sake of her pride.

Iris crossed her legs as tight as she could, keeping her hands pressed to her lap all the while, but she knew that it was no good. The others were only just starting to show signs of desperation, while she was barely hanging on. She wasn't going to win, and she knew she wasn't going to win, and so when she felt herself begin to leak, she stood up, face flushed, as her body announced her defeat. The other girls couldn't help but stare as she began to soak her pajamas, trying not to show just how much she wished she hadn't lost so early on.

As a puddle began to form at her feet, she sighed, only enjoying the relief a little bit. The contest had been stacked against her from the beginning, and now she was out of the running for good. But May bit her lip as she watched, feeling her own bladder practically beg her to do the same. It wouldn't be much longer for her either, and she squirmed, looking to Misty and Dawn to see what state they were in and if she had any chance.

It was becoming more clear that the both of them were desperate, but May could also tell that she was going to have a much tougher time than them. She stood up with her legs crossed, jiggling her knees as she fought to hold on, and for a while, she managed to do just that. Tears stung at the corners of her eyes as she was pushed above and beyond her normal breaking point, and soon both of the other girls were standing as well, both doing what they could to hold back just a little bit longer.

Misty had her hands between her legs and Dawn was practically dancing in place, while May was doubled over, breathing labored as she fought the very last legs of her losing battle. But then she felt her body giving up, even as she didn't want to, and there was nothing she could do to stop herself from giving in, her nightgown becoming a bit wet on the front while her pee ran down her legs, puddling on the floor beneath her. She sighed, saying, “I guess I'm out too...”

Misty groaned, the sound of liquid hitting the floor almost too much for her to handle right now. She had been in enough positions where she'd had to deal with the sound of water with a full bladder, but it had never become anymore bearable, and right now was no exception. She grit her teeth, staring Dawn down as they both battled for their chance with Ash.

Dawn was proud to say she had at least definitely made it into second place, but she wasn't ready to give up yet. First place was still a possibility, still within her grasp, and she redoubled her efforts, clenching her muscles as she ignored her bladder's pleas to be emptied. She had to wait until she was with Ash, she reminded herself. This would be how she won him over.

But Misty was thinking the exact same thing, and no more willing to give up her chance at victory. She was reaching far beyond her limits and she didn't know how much longer she could last, but she put everything she had into it, biting her lip and urging herself on, thinking about the payoff if she could just manage to outlast Dawn. Victory was so close, so very close, and yet so far away, because no matter what she did, she couldn't stop it when she began to lose control.

Groaning, Misty felt her cheeks burn as her pajama shorts were flooded and she was overcome with a relief that barely registered in the wake of her humiliation. She had been so close, but as her bladder emptied itself, she lost all chance, and she could only hope that Dawn's seduction would work and that Ash would be keen on the idea of a harem. Otherwise, she and the other two girls were out of the running for his affection forever.

Dawn would have been a lot more thrilled about her victory, had watching three girls wetting themselves not made it a lot harder for her to hold back. But she had to hold back because she had to go after Ash now and see if he even wanted something like this. It was their last effort to win him over, and it rested solely on her shoulders.

“Alright,” said Misty at last, “you won. You better get to Ash before it's too late.”

“Yeah,” agreed May. “Go for it! We'll clean everything up here.”

“Good luck,” added Iris.

“Thank you!” said Dawn, before beginning the walk to Ash's room, each step a struggle due to the fullness of her bladder.

 


	3. Chapter 3

It took a lot of slow, pained steps for Dawn to get to Ash's room with how full her bladder was, but she managed to keep herself in control the whole time, finally reaching his door. Ash was laying on his back, wearing only his boxers and sound asleep. Dawn stripped down to her panties and made her way to his bed, getting in with him and thinking about all that she wanted him to do to her.

She imagined him fucking her with her bladder full like this, imagined her being fucked until she couldn't hold it anymore, peeing uncontrollably as the two of them came together, and she couldn't resist touching herself. Dawn rubbed herself over her panties, and she made no effort to keep herself quiet; after all, she did want him to wake up and see her there, she wanted him to be enticed by her and finally give her the chance she had been waiting for for so long.

Moaning louder and louder, it wasn't long before the noise caused Ash to wake up, bleary, and it was clear by the look on his face that he had no idea what was going on. “Dawn?” he said. “What...what are you doing?” He had never in his life expected to wake up to one of his friends, nearly naked and masturbating in his bed.

Dawn replied, in a somewhat husky tone, “I'm just so desperate for your cock and I'm so desperate to pee...” She held his hand against her swollen bladder to emphasize her point, and though Ash still didn't understand what was going on, he quickly began to get hard, something that Dawn noticed immediately.

Taking his cock out of his boxers, she stroked him, getting him to a full erection in no time at all. “I've wanted you for so, so long,” she murmurs. “I've wanted this inside me for so long and I just can't wait for you anymore.” Not only that, she wasn't sure if her bladder could wait anymore, and she was so desperate in more way than one that she couldn't keep dragging this out, and so Dawn quickly removed her panties. Straddling him and positioning herself over his erection, she practically impaled herself on his member, crying out.

Ash was still too surprised to do much in reaction, and he moaned in sudden pleasure as he was engulfed in her warm folds. And the sudden penetration disrupted her bladder enough that a small spurt escaped onto him. Dawn didn't even really notice the pain of having her hymen torn, her over full bladder and her desire for Ash completely distracting her, and she cried out again, this time sounding much more pleasured. It was better than she'd ever dreamed, but it was all real, and she was going to make the most of every moment with him.

The fact that he had stopped questioning her and had never done anything to stop her and was still letting her have her way with him meant that she had actually won this time, that she was successful. Ash was hers, after so many failed attempts, after spending so much time thinking that she would never get this chance. Now she had it, and not only that, but she had gotten closer to the other girls through this and, if they were lucky, she had earned them their chance too. She felt such a strong solidarity with them that she couldn't help but grow more excited as she imagined Ash fucking each and every one of his admirers as a harem.

Her bladder kept aching for release and she kept ignoring it, riding him like she had no intention of ever stopping, and if she had it her way, she probably wouldn't. Her moans were getting louder and louder, and she had a brief thrill as she imagined if the girls could hear her all the way down the hall, if they could hear just how good Ash was making her feel, and how good she was making him fell. Her head tipped back, and she knew that it wouldn't be long for either of them, given the fact that it was both of their first time.

Ash mumbled her name a few times, the first thing he had really said since they had begun. It was taking him a bit of time to catch up with what was going on, considering how stunned he was by all of it, but he couldn't complain about it. Dawn was beautiful, and it was certainly something to wake up to her wanting him so much that she couldn't wait for him a moment longer. Just looking up at her was almost too much for him to handle, and he was almost there, biting his lip and moaning loudly.

Finally, it all became too much for Ash to handle, and he practically exploded as he came inside of Dawn, and this triggered her own orgasm in response. Not only that, but it meant the end for her bladder, and as she felt her walls contracting with her orgasm, she also felt a rush of hot liquid begin pouring out of her, soaking the two of them as she wet herself and they came together, just like what had happened in her fantasy before. It was so much better in reality, though.

There was a moment of silence as they came down from their pleasure before Ash finally spoke, finally able to process all that had happened. “That was amazing!” he exclaimed, and Dawn nodded in agreement.

“It was,” she said. “Better than I ever could have dreamed.” They were quiet again, and Ash had softened inside of her, but then Dawn grinned and said, “The other girls wet themselves too, you know. It was a contest to see who would get to come in here and seduce you. They're all waiting for you, and I think they'd enjoy a turn.”

Almost immediately, she felt Ash begin to grow hard again. “You like that? We'd all love a lot of turns with you, actually. We have a proposition for you, actually...” He wasted no time in getting up then, putting on a t-shirt and helping Dawn back into her pajamas, and then the two of them went back down the hall together.

 


End file.
